I sailed small boats from the time I was 8. This is invaluable. As an adult, I suggest that a one week or so intensive mono-hull class followed by joining a race crew on any boat that goes out weekly will teach you most of what you need. Find a boat where the beer stays on the dock and the skipper does not yell. You will likely start as a grinder or trimmer and will have the opportunity to move around and learn new stuff as you show aptitude and interest. This is sail school but its free and high intensity. Bring crew snacks or donuts.

I sailed small boats from the time I was 8. This is invaluable. As an adult, I suggest that a one week or so intensive mono-hull class followed by joining a race crew on any boat that goes out weekly will teach you most of what you need. Find a boat where the beer stays on the dock and the skipper does not yell. You will likely start as a grinder or trimmer and will have the opportunity to move around and learn new stuff as you show aptitude and interest. This is sail school but its free and high intensity. Bring crew snacks or donuts.

Excellent post. Sounds like we could be brothers.

BTW, I skippered my Ericson 35 in the wed night races and the beer did not come out until we crossed the line(usually first) ;-)

BTW, I skippered my Ericson 35 in the wed night races and the beer did not come out until we crossed the line(usually first) ;-)

Nice boat. I raced a Heritage One Ton for 18 years with the same 8-person crew in Cleveland. We also usually won. 3rd pl. boat of the year once. Beer stayed in coolers with the grilling stuff on the dock till after the race. We took nothing that would add unproductive weight. We were serious about our craft but we had a lot of fun. I still am in touch with nearly all of the old crew 20 years later.

Take the sailing lessons. Ultimately it may save your life. If you are in the forces you already know how well you are trained for your job. Now, imagine giving a green horn your job and telling them to just read a book and do it.

It would even be worth buying a small trailer sailor, then sailing every weekend once you have done your initial courses. The experience will be invaluable in the mean time.

For offshore sailing you will ultimately need to do a nav and seamanship course. But in the mean time, get into a basic course- together if possible. The next step would be to crew on OPBs (other peoples boats). The more boats the better as you will learn good and bad from each skipper. Even Racing. Racing will hone you sailing skill s very quickly. Your local sailing club will most likely have a list of boats seeking crew.

Cat vs mono is a personal choice. There are lots of threads here discussing the good and bad of each. But you could Charter one of Each for a few days and see what you love about each one, Plus it will give you more experience.

And just to double up,, Definitely get lessons!

What he said.

Jumping into a cruising cat with no experience is a setup for a disaster, unless you are exceptionally lucky or exceptionally smart. (Prob need both).

Thanks for all the info! While I/we are in CO, I will look into sailing locally and take some time off for week-long lessons. I do not want to rush the issue and we have plenty of time to learn. I just want to make sure the "schooling' that we do is value added and provides tangible benefits. It sounds like we need to be patient and incrementally increase our knowledge and experience. This (sailing)sounds so cool! I have always dreamed of sailing around the Caribbean - it has got be very liberating "hobby" and much more relaxing than dealing with international air-travel.

My wife and I are retiring from the military soon and are looking forward to sailing in the near future. The problem is the only boats I've captained are my 12' john boat and a 17' canoe. Are sailing schools worth the money any and time? Our goal is to sail around the Caribbean. Also, based on the research I've done on the internet, I am leaning towards buying a catamaran vs a mono. any words of wisdom appreciated!

Don't make the mistake I made. Years ago, I also went on a sailing course, got my ticket and was pumped with confidence. Prior to this, we have never been on a boat. The very next week, we went sailing in our brand new catamaran in hectic weather. The result was that I almost got arrested, coming back in I almost wrecked a couple of other boats in the marina, scaring the daylight out of several people and making a big idiot of myself. The reality was that we did not know enough, the trainers boosted our confidence beyond all logic and I, the idiot really thought that we were ready.

There is nothing more valuable then getting experience and keep practicing until you have mastered the technique, procedure or maneuver.

I sailed dinghies, Sunfish, Sailfish, Super Porpoise, Buccaneer, 505, 470, Prindle Cat, Hobie growing up. I spent many hundred hours in boats where you learned with little chance of injury or damage. Once married, I joined a race crew. I recommend this as the best fast track high intensity 'school'. Find a skipper who does not yell and a crew that leaves the beer on the dock and you will learn a lot. Consider getting yourself a Hobie 16 to 21 or a Prindle so that you can learn to operate jib & main on a cat. A Used older model of one of these cats is often available on a trailer at affordable prices and you will resell it later. I currently have a Tornado cat with a spinnaker in addition to our ketch. This cat is pretty intense and best suited to inland lakes with small waves. The Prindle 18 would be my recommendation. Unlike the Hobie, its hulls are less prone to pitch-pole & submarining. If capsized, the Hobie 16 and Prindle can be righted. by one or two crew. Some of the larger cats need help.

Don't give up. I thought we knew most of what we needed when we bought our 58 foot ketch but by the third outing we were ready to quit. Docking and close maneuvers were killing us. Had to learn patience - new for me.

Even inexperienced folks often have little problem getting a sailboat to move. Just raise the sails and secure that line at the bottom of the boom. In a couple of hours things will get much easier.

Problem is once the sailing is over you have to do something. I mostly single hand and it usually takes me at least half an hour to anchor, sometimes more.

Anchoring starts with making sure you have the right ground tackle. Lets not turn this into a which anchor is the best thread and let it go at you need a good anchor. Also chain and the right line securely attached to the boat. Next you need to find a good spot to anchor and get the boat correctly oriented to the wind and waves. I have an electric windless, but how ever you do it don't let out so much chain that it covers the anchor and prevents the anchor from getting a good start at holding. Once the boat drifts back and the chain starts to get a little tight let out some more, I will probably repeat this two or three times. Once I have let out enough scope I take a well deserved rest for a couple of minutes and watch how the boat is riding. Then I go to the anchor locker and get out the bridle, which is a must for me with a catamaran and a good idea for a monohull. It takes maybe five minutes to put the bridle on and adjust the lines on the cleats. Again it is time for a rest and just watch how the boat is riding. Then walk back to the helm, put the boat in reverse and back down. Lets just agree you need to back down and not argue about for how long and how hard. Now it is time to grab the iphone and start up Drag Queen, or what ever method you like to alert you to dragging. Sometimes it is also possible to take a visual assessment of trees, pilings, or whatever else is around as a backup to determine if you are dragging. After another short rest I will kill the engines. Then walk around the boat just to check out things again.

This may seem kinda long, but keep in mind you will spend way more time at anchor than you will sailing. If you are not the best sheet trimmer or navigator (and with several modern GPS units on the boat it is hard not be an adequate navigator) you will only wind up a little late getting there. If your anchor drags you may wind up aground on a soft sandbar at best.

I will be the dissenting opinion here. Cats are easy to sail. They don't heel which is the thing that really intimidates most novices. And they will motor turn a 360 in their own length or close to it so close quarters maneuvering is easier than a mono. You can go to the Carib and charter one with absolutely no sailing experience at all. The charter staff will give you a quickie lesson and send you off. You can do this.

These guys bought a cat and sailed around the world with no experience at all. Start reading the very beginning of their blog in the archives.Bumfuzzle

One problem with the cat/mono debate is that some cats are easier/harder to sail than others and the same for monos. More importantly you can get in trouble on both.

Not everyone has the same definition of sailing. Racers focus on stuff like selecting the right sail, trimming it right, and finding the course with the best VMG. Often times a race boat will be towed out to the race and just have minimum ground tackle. On the other hand lots of cruisers probably have the sails up less than one percent of the time. The real skills are things like making sure all the systems work and that boat is secured to the dock, ball, or anchor.

For most folks moving the boat with the sails are up is the easy part, as long as they have enough sense to sail in the right weather window.

The first rule of cruising is "I would rather be at anchor and wish I was at sea than be at sea and wish I was at anchor".

Maybe the wife is right, she thinks cruising cats are like bikes with training wheels

Cats and mono are different in several key aspects. Best to know the differences before you head off into the deep blue. Sure, you can wing it and survive like Bumfuzzle, because modern boats are strong and forgiving, but much more prudent to be prepared rather than just lucky.

I also know a couple of newbies who just winged it and in both cases lost their boats, but fortunately not their lives...Bumfuzzle just has a better blog.